Stereospecific production of 6- or 7-carbon-substituted-.beta.-lactams
US4237051A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Apr 19, 1979 |
| Grant date | Dec 2, 1980 |
| Priority date | — |
| Expiry date | Apr 19, 1999 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D499/00
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Reaction of 6- or 7-diazo-.beta.-lactams with allylic halides in the presence of a catalytic amount of metallic copper or a copper salt affords 6- or 7-carbon-substituted-.beta.-lactams with the desired stereochemical configuration at the 6- or 7-position. Subsequent reduction with a trialkyl stannane affords useful intermediates for further syntheses affording 6- or 7-carbon-substituted-.beta.-lactams. The present invention relates to a process for the production of 6- or 7-carbon-substituted-.beta.-lactams having the desired stereochemical configuration at the 6- or 7-position. More particularly, this invention provides a process for the preparation of a .beta.-lactam of the formula ##STR1## wherein R.sub.1 is cyano or COOR.sub.2 wherein R.sub.2 is a readily removable ester-forming moiety, hydrogen or an alkali-metal cation; PA0 R.sub.3 and R.sub.4 are independently hydrogen, lower alkyl, aryl or aralkyl; PA0 Z is a group of the formula ##STR2## wherein R.sub.5 is hydrogen, lower alkyl or aralkyl; and the dotted line indicates the optional presence of a double bond; which comprises PA1 (1) reacting a diazo-.beta.-lactam of the formula ##STR3## wherein Y is a sulfur or an oxygenat…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.